


Winner Take All

by rowdyhooligan



Category: Supernatural
Genre: Explicit Language, F/M, Fellatio, Masturbation
Language: English
Status: Completed
Published: 2018-12-06
Updated: 2018-12-06
Packaged: 2019-09-12 12:03:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,280
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16872597
Author URL: https://archiveofourown.org/users/rowdyhooligan/pseuds/rowdyhooligan
Summary: Dean discovers that losing a bet isn’t always a bad thing.





	Winner Take All

**Author's Note:**

> cross-posted from tumblr: written for @melissaj616 Birthday/ 1000 Follower Challenge. My prompt was #24 “Sugar, don’t start something if you don’t intend to finish it.”

“You sure about this, sweetheart? There’s no shame in backing down- as long as you don’t mind washing all the dishes for the next month.” 

“Why would I back down, Dean? This is in the bag…hope you’re ready to do all the laundry.” 

Dean rolled his eyes at your words. “Sugar, don’t start something if you don’t intend to finish. This is your last chance; no calling a truce halfway.” 

Scowling at his cocky attitude, you shot back, “Pick up your damn gun, Winchester.” 

It was late, too late for this little pissing contest with Dean. But with Sam gone on a visit to see Eileen, Cas off bonding with Claire on a salt and burn, and no new cases that needed solving, it was just you and the elder brother locked away in the bunker with too much time on your hands. What had started as friendly competition to keep yourselves occupied by seeing who was better at darts quickly devolved into who was the better marksman. How were you to have known that he would take losing so poorly? That was how you found yourself in the shooting range at two o’clock in the morning. 

“Alright,” he said, shrugging his shoulders and taking his place in the stall next to you. He put on a pair of earmuffs, identical to your own. “Don’t say I didn’t warn you.” 

A few minutes later, you set your gun down with a grin, your smirk growing wider at the petulant frown on Dean’s face. He scowled down at the paper in his hands, his frown getting bigger the longer he studied the bullet riddled silhouette. He studied his target, looked over at yours, studied his again. There was no denying it: your shots were better. Every single one of your shots hit the center of the silhouette’s forehead, whereas two of Dean’s were off by an inch. 

He glared at you. “Best two out of three.” 

“Face it, Winchester, you lost. Again.” 

“Come on, give me a break. I’m just a little high strung is all…I’ve been under a lot of pressure lately.” 

“Try not to take it so hard, Dean; I learned to shoot from my daddy, and he was the best damn marksman I’ve ever seen.” Setting your gun aside, you gave an exaggerated yawn. “Thanks for taking over laundry duty- it’ll be nice to sleep in tomorrow. Oh, and Dean, Sam usually forgets to add his boxers to the laundry hamper, so you’ll probably have to go digging around for those.” 

“Just one more shot, winner takes all,” he insisted. 

His less-than-graceful attitude was hardly a surprise to you by this point; competitiveness was a trait you shared, and it wasn’t uncommon for the two of you to get roped into some kind of bet. You generally took your losses in stride, using them to learn and hone your skills for the next time. However, that didn’t mean you weren’t intrigued by the idea of a second match. Looking him over, a stray thought crossed your mind- a fantasy really, of helping Dean ‘relieve’ some of that tension by going down on your knees and blowing him until the every last worry faded from his mind. 

You’d be lying if you said the thought of this had never crossed your mind before, the idea of taking Dean into your mouth, sucking him off until he was begging for release. It was a dirty little daydream that had gotten you off more than once in the past. As immature as he could be at times, you had to admit that in another life- an apple pie life- he would have been exactly the type you’d go for: handsome, funny, and kind of a smartass. 

Cocking your head to the side, you nodded to yourself, decision made. Maybe he’d be up for it, maybe not, but something told you he wouldn’t object to your terms. The way he looked at you when he thought you wouldn’t notice…yeah, he definitely wouldn’t object. “Winner take all huh?” 

He brightened at your response. “You got it sweetheart. You’re not afraid are you?” 

“I’m not the one who just got his ass handed to him,” you pointed out. 

He rolled his eyes. “Whatever. So, you in or what?” 

“I’m in.” 

His cocky attitude came back full force. “Well alright then. What are your terms?” 

“When I win,” you began, looking him over hungrily, “I get to suck you off.” 

Dean’s eyes widened in shock. “Excuse me?” 

In for a penny, in for a pound. “You heard me, Winchester- when I beat you again I’m gonna go down on you. Don’t tell me you’ve never thought of it.” 

He had the good grace not to deny it. “You sure about this?” 

“Wouldn’t have suggested it otherwise. Unless you’re not interested.” 

“Oh believe me, princess, I’m interested. But what do I get if I win?” 

“On the off chance you actually manage to…whatever you want.” 

His gaze darkened immediately. “You’re on.” 

Taking up your gun again, you adjusted your earmuffs back into place as Dean hurriedly set up new targets and returned to the stall next to you, his eyes flicking to you constantly. Adrenaline and anticipation chased away the sleepy heaviness in your limbs, your mind sharp and gaze focused as you took aim and fired; a hole appeared dead center in the target’s forehead. Putting your gun down, you looked over at Dean expectantly, raising an eyebrow in silent challenge. Even if he did manage to beat you in this absurd little bet, you both won in the end. 

Dean raised his gun, eyes darting over to you, then back to the target. You saw the determination there, the resolve to win…whatever he had in mind must have been pretty damn interesting, to say the least. You almost regretted your perfect shot now, intrigued by what he would have asked for as a prize. He licked his lips, sending a pulse of desire fluttering through your center. With a deep breath, he fired. 

And missed the mark by less than half an inch. 

“I toldja Dean,” you purred when he removed his earmuffs with a heated look, “my daddy was the best marksman I’ve ever seen: he taught me well.” 

“Sugar, don’t start something if you don’t intend to finish it,” he warned when you sidled in close, his Adam’s apple bobbing as he swallowed hard. 

Spurred on by the heat in his voice, you sank to your knees, keeping your eyes locked on his as you reached for his belt buckle. Working it open and popping the button of his jeans free, you took your time with his zipper, easing it over the growing bulge. Breaking eye contact, you peeled back the straining denim, catching a peek of coarse, curly hair trailing down to his boxers. Dean watched as you tugged his jeans down to pool at his pool at his ankles. 

The hard outline of his cock was visible through the fabric of his boxers. You slipped a hand inside to very gently wrap your fingers around the hard length of him. Dean sucked in a harsh breath as you pulled him free of the confining cotton, leaning back to grip the ledge for support. Panties damp with slick heat, you gave him a few experimental pumps, working him to full hardness. The weight of Dean’s eyes on you was exhilarating, the heat in his eyes shooting straight to your core. 

Working your hand up and down the silky steel of his cock, you flicked your eyes up to watch him watching you. Using your thumb to trace the prominent vein on the underside of his length, you dipped your head down and allowed the heat of your breath to hit the head. You didn’t take him into your mouth just yet, teasing him with the promise of what was to come. 

“Please,” he moaned out, his thigh trembling under your touch, “please.” 

Lips curling up in a smug grin, you were more than happy to oblige, your tongue flitting out to lick at the underside of the head. Dean gasped as you pressed wet, open-mouthed kisses all along the shaft, licking here and there, delighting in the salty tang of his skin. Tasting and teasing, the sounds he made got you wetter than ever; your panties were going to be soaked through in no time at this rate. 

It wasn’t long before you got impatient, tired of waiting for the main event. Wrapping your lips around the head of his cock with a moan, you let your eyes slide shut as you took him into your mouth. Dean let out a groan, one of his hands going to cradle the back of your head. He didn’t try to force you down, content to let you set the rhythm. Sucking steadily, the weight of him pressed down on your tongue with every bob of your head. 

Giving him one final pump, you pulled his boxers down his thighs, cupping his exposed balls and giving a gentle tug. Dean let out a loud moan, his cock jerking hard in your mouth. You did it again, earning a hissed “Fuck”. You grinned around him; If he liked that, he was really going to enjoy this next part. Taking a deep breath, you relaxed your throat and took him down to the root, the prickly curls of hair tickling your nose. 

“Jesus, sweetheart,” he groaned, his fingers tightening against your skull. 

Holding yourself in place, you ignored your watering eyes and the saliva pooling at the corners of your mouth, forcing down the desire to gag. Darting your tongue out, you lapped at the soft skin of his ballsack. Heat radiated from Dean, heat and musk and need. He actually whimpered when you swallowed, the muscles of your throat constricting around him. Only the need for air had you pulling up, wiping at your eyes with the back of your hand. 

Without giving him a chance to catch his breath, you started sucking on him hard and fast, caressing and massaging his balls in time to your mouth’s movements, determined to hear him beg for you. Salty spurts of precome coated your tongue, fueling the ache between your legs. Your panties clung to you, slick with arousal; you squeezed your thighs together in a desperate search for friction. 

The wet slurp of your mouth echoed through the room, joined by your breathy moans and Dean’s harsh panting. His cock felt like it was swelling in your mouth, his balls drawing up in anticipation. Finally giving into temptation, you reached down to slide a hand inside your shorts, past your panties, and thrust two fingers inside your soaked pussy. Fucking yourself on your fingers in time to the frantic bobbing of your head, the first sweet pulses of orgasm rippled through you just as Dean cried out your name, curling in on himself as he came down your throat. 

Your pussy throbbed as pleasure overtook you, heightened by Dean’s own release. Come coated your tongue as you swallowed his essence down, every bob of your head coaxing him along, urging him to give you all that he had. The clench and release of your pussy walls echoed the twitching of his cock as steady jets of come continued to fill your mouth. Some of it trickled out the corner of your mouth before you could swallow it, there was just so much; he hadn’t been kidding when he said he was high strung. Holding your fingers as deep inside you as you could reach, you rode out the waves of ecstasy. 

Gradually, the spurts of come slowed to a stop, Dean’s cock softening in your mouth. It was with great reluctance you let him slip from your lips before he got overstimulated, giving him one last kiss on the head of his cock. Your fingers were drenched with your release when you pulled them free of your channel; you surreptitiously wiped the sticky mess off on your thigh. Brushing away the come from the corner of your mouth with your thumb, you hummed in satisfaction when you popped it into your mouth. The two of you took several minutes to catch your breath, incapable of words. 

Glancing up at Dean, you noted with smug satisfaction the blissed out look on his face, his cheeks flushed and a smile tugging at his lips. He looked utterly debauched with his pants around his ankles, boxers pulled down just enough to leave his cock and balls exposed, glistening under the florescent lights of the shooting range with saliva and come; you were certain you didn’t look much better. You really should have done this ages ago. 

“Well, that was fun,” you said, rising to your feet with a stretch, ignoring the pain in your knees. 

“Where,” Dean cleared his throat before continuing, husky voice even more gravelly than normal, “where are you goin’?” 

“To hit the showers before bed,” you answered with a slight smile, spinning on your heels and heading for the bathroom. 

“Oh yeah?” he called out after you, “You want any company? Cuz sweetheart, after feeling that sweet little mouth, you’re giving me all sorts of ideas.” 

Casually, as if you didn’t care one way or the other, you tossed over your shoulder, “You’re welcome to join me if you like, but Dean…don’t start something if you don’t intend to finish it.” 

You smirked to yourself at the sound of his belt jingling and the harsh zip of his zipper, the heavy thud of booted feet trailing in your wake.


End file.
